


V-card

by Merciignoremoi



Category: Video Blogging RPF
Genre: Anal Fingering, Anal Sex, Daddy Kink, First Time, Gay Sex, M/M, safe sex
Language: English
Status: Completed
Published: 2021-01-06
Updated: 2021-01-06
Packaged: 2021-03-16 15:40:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 2,356
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28584396
Author URL: https://archiveofourown.org/users/Merciignoremoi/pseuds/Merciignoremoi
Summary: Wilbur takes Tommy’s v-card
Relationships: Wilbur Soot/TommyInnit
Comments: 13
Kudos: 260





	V-card

Tommy’s parents were gone for the weekend, and he wanted to have some fun. He had never had sex before, and wanted to try it.

So, who better than to give his v-card to than his older friend?

Okay, maybe not the best idea he’s ever had, but you get the point.

He’s had a crush on Wilbur for months now. The older man catching his attention one day after a stream. Some older fans were being creepy in chat, and Wilbur, always one to play along, said “hey! That’s MY 16 year old boyfriend!”

He laughed it off, saying it was a joke but Tommy had found himself secretly wishing it was true. He knew it could back fire on Wilbur very badly, but he wanted it so bad.

So, that weekend he had planned to invite Wilbur over to hang out. Of course the older man said yes, saying he’d be there around 1pm.

He had set out some snacks on his desk, a few waters near by. He also hid some lube and a pack of condoms just out of sight. He pulled up his Disney plus account, putting on lilo and stitch, Wilbur’s favorite as said in a stream.

*KNOCK KNOCK*

There was a pounding on the door. “Coming!” Tommy shouted excitedly, rushing down the stairs.  
He flung open the door to reveal Wilbur in his usual yellow sweater and black jeans, fluffy brown hair tucked away under a beanie. They smiled at each other.

“Hey man! What’re we doing?” Wilbur asked, stepping inside.

“I’ve got some snacks and Disney plus set up in my room. Lilo and stitch is pulled up.” Tommy grinned.  
Wilbur’s eyes went wide. He raced up the stairs to where he knew Tommy’s room to be.

Tommy laughed and followed him. They flopped down on the bed together.

The bed was quite small, only a twin, so they had to cuddle with each other. After a few moments of shifting to get comfortable, Tommy started the movie

————Line break————

About half way through the movie Tommy had begun to get impatient. He wanted this to be a nice time, he really did, but he was impatient.

He sat up, turning to face Wilbur.

“Tommy? Is something wrong?” The taller man asked, a puzzled look on his face.

Tommy took a deep breath. “There’s another reason I wanted you to come here.”

Wilbur was confused, another reason? What could that be?

“I’ve been thinking, and I’ve made a decision.”, he paused to collect himself, “I want you to fuck me.”

The older male was in shock, and just as he was about to say something, Tommy spoke again.

“And no, this isn’t some elaborate prank, or me pulling your leg. I want to have sex with you. I’m 16, and that’s the age of consent, I looked.” He said, looking Wilbur in the eyes.

Wilbur couldn’t believe it. He just couldn’t. So, just when the silence had become too much, he spoke up.

“Are you sure? I don’t want you doing something you’ll regret.”, Tommy nodded his head, “Come here, sit in my lap.” He said, patting his thighs.

Tommy nodded again, obeying Wilbur’s words. It was out of character for him, to be so obedient.

“Do you know how this works? Or do you need me to guide you?” The taller man asked, studying his much younger partner’s reaction.

Tommy bit his lip, “I...I’ve read fan fiction.” He stutters out.

Wilbur shakes his head, “Tommy, fan fiction isn’t a good place to get your sex tips. It’s not realistic.” He scolds. “It looks like I’m gonna have to show you how to do this.”

Tommy looks down, a heavy shade of pink tinting his cheeks in embarrassment.

“Hey, it’s okay. It’s your first time, there’s no shame in not knowing. I didn’t know how to do this the first time either.” Wilbur says, lifting the younger’s head to look him in the eyes. “I’m glad you chose me to be your first. I’ll be gentle with you.” He reassured, a soft smile on his face.

Tommy smiled back and leaned in for a kiss. It was sloppy and unsure, but he was new to it. Wilbur tilted his head into the kiss, guiding it, deepening it. They pulled back for air, panting.

“That was my first kiss.” Tommy panted, blue eyes darkening with lust. Wilbur shuttered in arousal. That shouldn’t turn him on that much.

He shouldn’t be doing this. He was an adult. He could catch a case for this.

“Wilbur? Are you okay?” Tommy asks, eyes darting around, looking for something.

“I’m fine. I should be asking you that. I’m the adult here.” Wilbur reassures, and dives back in for another kiss. This one is much hotter, deeper, than the last.

Tommy is responsive, letting out little gasps here and there. Wilbur licks the younger’s lip, asking for entrance, which Tommy grants. The kiss becomes heated and heavy. They pull back, a line of drool connecting their lips.

“Now, I have a question for you. Is there anything you wanna call me? Daddy, sir, etc? Or do you just wanna call me Wilbur?” He asked.

“Uh...can I call you daddy? And...can you call me stuff like, baby or sweetheart? I don’t know why, I just really like that stuff.” Tommy said, getting even redder, which Wilbur didn’t think was possible.

“Of course, baby. Daddy will take good care of you. I promise.” Wilbur coos, a smile gracing his lips.  
He kissed his neck, biting down softly. Tommy gasped “Daddy!”

“Shh...it’s okay, little prince. Did you like that?” Wilbur smirked. He ran his hands up and down Tommy’s sides, bunching up his shirt.

“Off.” He ordered, Tommy quickly complying. The older man marvled at the pale skin being exposed, smooth and untouched. He went back to kissing his neck, sucking and biting, leaving small marks that were easily covered.

Tommy whined and pulled at Wilbur’s yellow sweater. “Do you want me to take it off? Use your words.” He said.

“Please...take it off, wanna see you.” Tommy whined, bouncing with all the impatience of a teenager.

“Good boys don’t whine.” Wilbur scolded, pulling off the offending garment. He went back to trailing hickies down the boy’s body. He caught a nipple between his fingers, twisting it. This earned him a gasp.

He continued playing with the boy’s nipples, pinching and twisting, licking at them to soothe him. Tommy moaned, breath catching in his throat. He buried his hands in Wilbur’s hair, pulling.

“Fuck...”, Wilbur breathed, “Keep your hands right there, baby, don’t move ‘em. Daddy likes it when you pull his hair.” He said, biting down harder on Tommy’s collarbone.

“Daddy! Oh, daddy please...” Tommy moaned, throwing his head back.

“Hmm? What, baby?” Wilbur hummed, not looking up from what he was doing.

“Daddy...daddy, please...need you..” the younger boy moaned, grinding down onto Wilbur’s lap.  
Wilbur grabbed his hips, stilling them. Tommy whined, trying desperately to move, get some kind of friction on his dick.

“C’mon little prince, tell daddy what you need.” Wilbur said, massaging his hips.

“Please...fuck me! Fuck me, daddy!” Tommy shouted as Wilbur rewarded him with a hand on his crotch.

“There’s my good boy. Do you have lube? Or condoms? We can go without if you don’t. I’m clean, and you’ve never had sex.” Wilbur praised.

Tommy nodded, grabbing the lube and box of condoms from his desk. After dropping the items on the bed, he pushed down his pants and boxers in one swift motion. He flopped down on his back in front of Wilbur, spreading his legs as wide as he could manage.

Wilbur’s eyes widened, a smirk forming on his face. “Good job, baby boy. You even know how to spread your legs for me. So good.” He praised, kicking off his jeans and boxers.

When Wilbur’s dick sprung free of its confines, Tommy became worried. He had seen enough porn to know Wilbur was big. How would that thing fit inside him? It had to be least 10 inches or more.

Noticing the worried look on Tommy’s face, Wilbur spoke up. “Are you okay? Do you want me to stop? I can go take care of this in the bathroom.” Wilbur asked, he was eager to be inside the boy, but he didn’t want to hurt him.

“No! I’m fine. It’s just...” He trailed off, looking back down at Wilbur’s dick, eyes impossibly wide.

Wilbur looked down, took a deep breath, and laughed.

“Hey! That’s not funny! You’re dick is huge! How is that...THING going to fit?!” Tommy shouted, turning even pinker.

“Haha, sorry sweetheart. It’s just...it sounded, and looked, like something out of a cheesy porno. It’ll fit, don’t worry. I just gotta prep you.” Wilbur said, bringing a hand up to cup Tommy’s face. Tommy leaned into the touch and sighed.

“Okay. I trust you.” Tommy said, looking up at Wilbur with adoration.

Wilbur’s breath hitched, he nodded, and grabbed the lube. He slathered three of his fingers with the substance, and capped the bottle. Tommy layed back down, spreading his legs.

“Here, bite down on this.” Wilbur said, stuffing his boxers in Tommy’s mouth. Tommy made a noise of surprise, an affronted look on his face.

“Oh, hush. It’s so you don’t bite your tougne from the pain.” Wilbur said.

Tommy settled back down, looking up at Wilbur. He strangely didn’t mind the boxers in his mouth. He could smell him, fresh clean soap and just a hint of something all it’s own. He could taste Wilbur too, although faint, it was heavenly.

Tommy gasped as he felt a finger press at his entrance, it was cold. “Sorry.” Wilbur quickly apologized, kissing along his thighs to take his mind off it.

Tommy screamed and bit down, hard, when the first digit entered him. He was glad for the boxers. He squirmed and twisted, trying to make it stop hurting. After a few moments, it stopped hurting, and Wilbur slowly moved his finger in and out.

Soon enough, he added a second and third, both going in much easier than the first. He kept feeling around, looking for that spot that would make the boy scream. And then he found it.  
Tommy moaned, arching his back. 

He spit out the boxers and asked, “W-what the hell was that?”

Wilbur chuckled, “That was your prostate. It’s like a girl’s g-spot. Feels good, aye?”

Tommy nodded, he pushed back against the fingers inside him, wanting more of the feeling.  
“Shh...baby, it’s okay, daddy’s got you.” Wilbur cooed, kissing Tommy’s forehead. He pulled his fingers out, Tommy whining at the loss.

“Shh...hey, your gonna get something much better in a moment.” Wilbur said softly.

This made Tommy nervous again. Was it gonna hurt? Would he tear? He heard about that happening.

No. Wilbur had him, he was okay.

Wilbur picked up a condom, but Tommy stopped him. “You, Uh...you can go without it...if you want.” He stuttered, looking down.

“Are you sure? Do you want the condom? This is about you Tommy, not me.” Wilbur said, looking Tommy in the eyes.

“No, I don’t wan’ it. Wanna feel you, daddy.” Tommy mumbled, looking away.

“Okay, my special little prince.” Wilbur said, running his hand through the younger’s hair before slicking up his cock.

He lined up with the boy’s entrance, slowly pushing the tip in. Tommy hissed in pain, clenching his teeth.

“Shh...it’s okay, daddy’s here. I’ve got you.” Wilbur cooed. It continued like this for several minutes. Wilbur pushing in a little, Tommy hissing in pain, and the older man cooing at him and making soft noises.

After a good ten minutes, he finally bottomed out. He was so tight and warm, so perfect.

“Daddy...daddy it hurts.” Tommy cried, tears pricking at the corners of his eyes.

“Shh...I know baby, give it a few more minutes, then it’ll feel good. You just gotta adjust.” He tried soothing the younger boy, but to no avail.

Tommy cried in pain and Wilbur was there to dry his tears. He kept cooing softly, whispering sweet nothings and praise in his ears. “You’re doing so good baby, daddy’s so proud of you.” Wilbur cooed.  
After what seemed like forever, the pain started to go away, slowly being replaced by pleasure.

“Daddy...you can move now.” Tommy panted.

Wilbur slowly pulled out and pushed back in again. It started hurting again, but soon was replaced by pleasure as Wilbur found a rhythm. Tommy moaned and panted, little ‘daddy’s and ‘please’ coming out of his mouth.

“Daddy, please-ahh! Faster!” He moaned, pushing back against Wilbur’s thrusts.

Those words broke his resolve. He grabbed Tommy’s legs and pushed them up to his chest, dick hitting him impossibly deep. It made Tommy scream. With every thrust, he was hitting the boy’s prostate.

“Fuck, you’re so tight, baby. So good for me. Such a good boy for daddy.” Wilbur practically growled out. Tommy keened at the praise. Wrapping his legs around Wilbur’s waist, he tried pulling him in even deeper.

“Ahh-fuck, daddy! g-gonna cum...” Tommy moaned.

“Cum. Cum for me, baby boy.”

And that was it, Tommy came. His eyes rolled back in his head, mouth forming a perfect ‘O’, with his tougne hanging out slightly. Wilbur thought he looked like a hentai character. A few thrusts later he came as well, spilling inside the boy beneath him.

They lay there panting. Wilbur pulled out, feeling some of his cum leak out of the boy’s hole. He looked down and groaned at the sight. He looked so ruined, covered in his own cum, Wilbur’s leaking out his ass. To Wilbur, he looked like the perfect whore.

He flopped down next to the boy and pulled him close.

“Did you like that, Tommy? Was that okay?” Wilbur asked, picking up his boxers to wipe Tommy off with.

“I loved it, Wilbur. I’m glad I chose to give my v-card to you.” Tommy said, looking up at him.

“I’m glad too.”

**Author's Note:**

> Thank you for reading! This was a commission from someone on twitter!


End file.
